1. Field of the Invention
This invention relates to a structurally unique group of macrolides and, more particularly, to derivatives of oleandomycin, its 11-mono- and 11,2'-dialkanoyl esters having at the 4"-position an amino group substituted with an alkylene group having from 1 to 4 carbon atoms and at its end position a group of the formula --Z--R wherein Z is O, S, SO, SO.sub.2, &gt;CO, CHOH or NH; and R is a phenyl, substituted phenyl, pyridyl, 2-pyrimidinyl, 2-(1-methyl)imidazolyl or chloro substituted pyridyl group, and to methods for their preparation. The compounds are antibacterial agents.
2. Description of the Prior Art
Oleandomycin, a macrolide antibiotic produced by fermentation, was first described in U.S. Pat. No. 2,757,123. It has the formula, the absolute configuration of which is shown below: ##STR1## It consists of three main structural features: the L-oleandrose moiety, the desosamine moiety and the oleandolide moiety.
Derivatization of oleandomycin has focused primarily upon the formation of esters at one or more of three hydroxy groups located at the 2', 4", and 11-positions. Mono-, di- and triacyl esters wherein the acyl moiety is derived from a lower aliphatic hydrocarbon monocarboxylic acid having from two to six carbon atoms are described in U.S. Pat. No. 3,022,219.
Aminohydrin derivatives of oleandomycin are reported by Kastrons et al., Khim. Geterosikl Soedin (2), 168-71 (1974); C.A. 80, 145986n (1974). The compounds, for which no utility is reported, are prepared by treating oleandomycin with a dialkylamine or a heterocyclic amine in a sealed tube for 20 hours at 30.degree. C. The epoxide moiety at the 8-position is the site of reaction.